Let's say that you are planning on taking 4 technical certification classes in the next couple years. All of the training is relevant to your current job, but some of it is on technology you work on daily and are very familiar with, while other training is stuff you will eventually be working on in your job, but you have zero experience with it right now. Which order would you take the classes? I am thinking I should take the classes that cover what I am doing right now, to give myself a better chance of passing the certification exam related to the class. The courses on technology I don't currently use will become more relevant in the future, when our company starts using those technologies.

I can see the other point though, in terms of maximizing current skillset, I would probably want to take the courses for tech I don't know anything about. That would make me better equipped to work with that technology when it does come to our company. Taking a class to cover stuff I already work on is a gimme.

Assuming these are required classes I would start with the things you know first so that you get into the groove of classes again. The easy stuff will make you comfortable with moving forward into the new topics you aren't familiar with. This of course assumes someone else is paying for the classes and you can't just skip out of the classes and take the tests for certification with some self study.

I've looked at some certifications from the local universities around me which are part of their continuing education program. The problem is that the intro classes are *way* too easy. Given that the classes are expensive, I'm not sure it's worth my $$$ to take the easy classes, just to take the hard later classes that are useful for me in the certification program.

Assuming it would be worth my money, I'd take the easier courses first to get a feel for what the certification - then move through the courses in the progression they've defined.

"Over the next couple years" + "some of it is new" = I would take the classes on the new stuff first. Why? Overall gain is higher - you're going to learn the new stuff and be able to better apply it NOW in a lab, testing, dev, and production while you're then going back and taking "refresher" classes over the next 18 months on stuff you already know.

I will be taking the courses for the CCNP Security certification. The courses are (roughly) IPS, Firewall, Routers/Switches, and VPN. Before joining my company's IT Security team, I was in the networking team as a Firewall Admin. For me, the order from easiest to hardest would be Firewall, Routers/Switches, IPS, VPN.

Take the classes you are familiar with first, and the classes new to you last.

Because I always could use a refresher, you get used to the coursework, the teacher, and so on. And to be honest, I don't know "everything there is to know about basic" whatever. Even on "Linux n00b" sites, I learn a few lines here and there. Some teachers give you a different spin on things, and it can be helpful to see something you've done a million times as "here's an easier way to look at it," and go, "Wow... that saves me a fuckload of time!"

The argument for doing roughly easy-to-hard includes the fact that it allows you to gain momentum. You get to achieve one of the intermediate goals early, and that should keep you motivated toward the longer term goals. If you work for a long time without any achievements, that can be pretty de-motivating. It's just human nature.